He appeared in the first season of the television show 24 as Carl Webb, played Andy Cramed, the gambler who brought the plague to town, on Deadwood, and appeared in several episodes of Law & Order. On film he played Edward Norton's boss in Fight Club and Mel Nicolai in Zodiac, both David Fincher films. He appeared in the 1988 movie Talk Radio as finance guru Sid Greenberg, a role that he played in the original stage version of the script. In the movie Twister, he played Eddie, Dr. Jonas Miller's assistant. He played Mr. Reilly, one of the Callahan Auto Parts associates, in Tommy Boy. He appeared in Donnie Brasco as a marriage therapist. He played a role of Professor Cardiff in an 2006 horror film Pulse.

In 2010, he was cast on the television series The Good Wife as David Lee, a senior attorney, a role that soon became part of the recurring ensemble. He was promoted to series regular at the start of the fifth season in September 2013.[5]